Synthesis of cis-vinyltrimethylstannanes and cis-vinylpinacolboronates in a two-step highly regio and stereoselective process

Paul Malek Mirzayans, Rebecca H. Pouwer, Craig M. Williams*, Paul V. Bernhardt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Citations (Scopus)

Abstract

A highly efficient two-step regio and stereoselective method for the synthesis of both cis-vinyltrimethylstannanes and cis-vinylpinacolboronates is described. This method takes advantage of the known lithium/tellurium exchange pathway providing a versatile alternative to known literature methods. The methodology presented demonstrates compatibility, for example, with substrates bearing oxygen functionality in comparison to previously reported methods of cis-selective hydrostannylation (i.e., ZrCl4).

Original languageEnglish
Pages (from-to)8297-8305
Number of pages9
JournalTetrahedron
Volume65
Issue number39
DOIs
Publication statusPublished - 26 Sep 2009
Externally publishedYes

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